HCID 10702957, compound → HCID 10584033, compound

HRID 1457394Notes

Reaction equation

HRID 1457394 reaction equation
[OH:1][C@@H:2]([P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9])[CH:3]=[C:4]([CH3:6])[CH3:5]>CO.[Pd]>[OH:1][C@@H:2]([P:7](=[O:12])([O:8][CH3:9])[O:10][CH3:11])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

4

Procedure

Dimethyl (S)-1-hydroxy-3-methyl-2-butenylphosphonate obtained in Example 31 (68% e.e., 54 mg) was dissolved in 10 ml of methanol, and 10% Pd/C (16 mg) was added thereto. The mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. The reaction mixture was filtered through Celite and the filter cake was washed with ethyl acetate. The solvent was distilled under reduced pressure and the residue was purified by flash column chromatography (acetone/hexane=1/4, on SiO2) to obtain dimethyl (S)-1-hydroxy-3-methylbutylphosphonate as a final product in a yield of 98%. This compound is known to be useful as a raw material for medicines and the like. The chemical reaction in this Reference Example is shown in chemical formula 49.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with ethyl acetate
  3. distillationThe solvent was distilled under reduced pressure
  4. customthe residue was purified by flash column chromatography (acetone/hexane=1/4, on SiO2)

Sources & evidence

ORD record
ord-a44adf988d6e46908e4f09b209e6a504
Source dataset
uspto-grants-1998_12
Patent number
US05847186

Reaction notes

Loading…